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Lakeville Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Lakeville vacation rentals

Coffee/tea maker, fridge, microwave, oven

1. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.0 out of 10, Very Good, (1 review)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
Cozy 1-bedroom studio in serene Great Barrington with AC
Property grounds

2. Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (8 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
The price is ￥12,608
￥21,030 total
includes taxes & fees
Aug 3 - Aug 4
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Interior

3. Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (13 reviews)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
United States
Tom S.
The price is ￥62,960
￥110,060 total
includes taxes & fees
Aug 3 - Aug 4
Guesthouse Cabin vacation rentals in Berkshire County
Terrace/patio

4. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (50 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is ￥19,832
￥33,667 total
includes taxes & fees
Aug 12 - Aug 13
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Smart TV, fireplace, books

5. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (20 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is ￥26,089
￥33,307 total
includes taxes & fees
Aug 2 - Aug 3
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Property grounds

6. Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"The accommodations were wonderful and comfortable."
United States
Chuck S.
The price is ￥17,314
￥32,585 total
includes taxes & fees
Aug 3 - Aug 4
Hoppy Hill Farm House
2 bedrooms, WiFi (free), bed sheets

7. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is ￥19,549
￥35,152 total
includes taxes & fees
Aug 5 - Aug 6
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Desk, iron/ironing board, WiFi, bed sheets

8. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is ￥23,610
￥29,969 total
includes taxes & fees
Aug 4 - Aug 5
The Brooks Motel: Exceptional Suite
TV, fireplace, books

9. NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
10.0 out of 10, Exceptional, (2 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is ￥44,843
￥125,544 total
includes taxes & fees
Aug 4 - Aug 5
NEW: Chic Modern Barn Style Home in Fun Area
Exterior

10. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.2 out of 10, Wonderful, (5 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
The price is ￥15,205
￥44,666 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Attic 10 min to Llitchfield
Outdoor dining

11. Glamping, family fun, pet friendly

Glamping, family fun, pet friendly
Dover Plains
10.0 out of 10, Exceptional, (4 reviews)
"Great Glamping spot. The hosts were very responsive and the place provided many activities. "
United States
Gui
The price is ￥12,608
￥21,030 total
includes taxes & fees
Aug 3 - Aug 4
Glamping, family fun, pet friendly
Dining

12. Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is ￥22,132
￥67,551 total
includes taxes & fees
Sep 1 - Sep 2
Art House 3 Beds Close to Warner Theater
Exterior

13. Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is ￥20,328
￥52,434 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Modern Farmhouse Private Apt - 3 Beds
Property grounds

14. Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly

Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly
Dover Plains
10.0 out of 10, Exceptional, (5 reviews)
"Fun place with a variety of activities including hot tub, miniature golf, corn bag toss, etc. "
United States
Tania
The price is ￥12,608
￥21,030 total
includes taxes & fees
Aug 3 - Aug 4
Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly
Smart TV, fireplace

15. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (19 reviews)
"Wow what an enjoyable stay! Clean, fresh, relaxing, and wonderful to meet owners Corin and Jen… gracious and hospitable hosts. Very comfortable, great location, well appointed… everything we were looking for!"
United States
James M.
The price is ￥25,184
￥43,324 total
includes taxes & fees
Aug 26 - Aug 27
Pristine Cozy Walkable Downtown 2BR Getaway
Coffee/tea maker, fridge, microwave, oven

16. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (35 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥42,498
￥64,348 total
includes taxes & fees
Aug 12 - Aug 13
Home in Great Barrington
Interior

17. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (21 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is ￥38,123
￥57,737 total
includes taxes & fees
Aug 30 - Aug 31
Cozy Riverside Berkshires Retreat
Desk, iron/ironing board, WiFi, bed sheets

18. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very Good, (6 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is ￥24,869
￥31,379 total
includes taxes & fees
Aug 2 - Aug 3
The Brooks Motel: Exceptional Suite
TV, fireplace, DVD player, books

19. Mtn-View Retreat in Huson Valley: Great for Groups

Mtn-View Retreat in Huson Valley: Great for Groups
Claverack
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful rental - spacious, beautiful views, and gorgeous home!"
United States
Samantha A.
The price is ￥29,749
￥117,761 total
includes taxes & fees
Aug 9 - Aug 10
Mtn-View Retreat in Huson Valley: Great for Groups
Exterior

20. Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
9.6 out of 10, Exceptional, (4 reviews)
"Lovely home in the heart of Millbrook."
United States
Marianne A S.
The price is ￥50,368
￥77,990 total
includes taxes & fees
Aug 3 - Aug 4
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Lakeville Hotel Reviews

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

10/10 Excellent
"Great experience this place is a hidden gem. Clean, quiet, convenient. Plus there is a pool. I hope to return sometime soon."
Jane 1-night trip
Posted 3 hours ago
Travelodge by Wyndham Great Barrington Berkshires

Find out more about Lakeville

Search for holiday rentals in Lakeville on Expedia! You can easily find your home rentals, villas, holiday apartments in Lakeville using one of the methods below:

  • View our selection of featured holiday rentals in Lakeville
  • Use the map to find apartments and other holiday homes in the Lakeville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Lakeville while they last

Look no further and take a look at our great range of rental properties in Lakeville!

Frequently asked questions

Can I find vacation rentals in Lakeville?

Yes, we offer vacation rentals close to well known attractions in Lakeville, or you can select a secluded option if you'd like a relaxing place to stay. Lakeville is known for its restaurants and museums.

What are some of the best vacation home rentals that Lakeville has to offer?

Cozy Riverside Berkshires Retreat: This vacation home near Lakeville is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Lakeville?

Expedia has 14 vacation rentals for your stay in Lakeville.

What’s there to see and do in Lakeville?

While exploring the area, visit family-friendly sights like Harney and Sons Tea Tasting Room, or get outside and enjoy nature at Harlem Valley Rail Trail. Holley-Williams House Museum and Lime Rock Park are other places to visit while you're in town.

What’s a vacation rental in Lakeville like?

A vacation rental is a private property you can book for a few weeks or just a few days in Lakeville. Vacation rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for family trips.